


Pretty Boy Drifters

by beansprean



Series: Rhonda Hurley is a Dom [2]
Category: Supernatural
Genre: Bottom Dean, Canon Compliant, Dirty Talk, F/M, Feminization, Like lots of it, PWP, Panty Kink, Pegging, Praise Kink, Sex Toys, Sub Dean, and some art history too, mild Dom/Sub, rhonda pov, stay in school kids, this also ended up being character meta whoops, this is so dirty dont even read it omg
Language: English
Status: Completed
Published: 2013-10-28
Updated: 2013-10-28
Packaged: 2017-12-30 09:33:01
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,362
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1017004
Author URL: https://archiveofourown.org/users/beansprean/pseuds/beansprean
Summary: <blockquote class="userstuff">
              <p>An older and sadder Dean shows up at Rhonda's door, needing something he thinks he can get from her.</p>
            </blockquote>





	Pretty Boy Drifters

**Author's Note:**

> Takes place sometime between 7x02 "Hello Cruel World" and 7x17 "The Born-Again Identity".

The last thing Rhonda expected was to find Dean Winchester on the other side of her door.

Since domming the fuck out of a pretty boy drifter who rolled through town like a tumbleweed, Rhonda had both changed and not. In the years that had passed between then and now, she cut her hair short and let it grow out again, had spent a fantastic and energetic summer with a shy girl named Laura, and was briefly engaged to a man who preferred her sister. Her father had two heart attacks and divorced her mom and Rhonda's art suffered in between them. She'd fallen in love with Hannah, an angel on earth, then got dumped when she wasn't loved back.

Either way, things had come full-circle; Rhonda was single and hurting and looking for sex that she couldn't fuck up. No pun intended.

Dean looked nervous, fidgeting on her doorstep and looking up with wide eyes when she called his name.

Rhonda grinned. "Dean Winchester. Taking me up on my offer after all these years?"

Good god, the man actually _blushed._

"Uh...well. Me and my brother were just, ahm. Passin' through. Thought I'd look you up." His shoulders were squared and he held his head high, almost cocky, but his gaze kept skittering away, down, submissive.

Rhonda stepped back to let him in without a thought.

 "So, um...you still doin' that...comic book...thing...?" Dean stuttered out while Rhonda went to the kitchen to get them some beers. She chuckled, not having entertained for a moment that he would remember a detail about her not related to sex.

"Yeah, sorta," she replied, returning to the living room to find Dean standing awkwardly on her rug. Rhonda thrust a beer in his hand and steered the poor man toward the couch. "A 'suffering artist,' as my mom calls it. You still doing that 'mysterious drifter' thing?"

"Heh, kinda," Dean replied. Then he was quiet, picking at the label of Rhonda's expensive German beer without drinking it.

Rhonda looked at him, studying his hard profile and the distance in his eyes. He wasn't just older - he looked tired, sad even. He wore a frown with a deep slash in his brow and a new squareness to his jaw. When she'd had him, he was a soft, slender thing with big eyes and a pretty mouth that she wanted parted around a moan. Now he was a big man who looked like he'd seen hell, and she wanted him warm and soft and begging beneath her like no one she'd had before.

She waited for him to sip halfheartedly at the beer before she spoke. "You know, if you're here for sex, I'm more than up to it."

Dean choked, spluttering around the neck of the bottle. Rhonda grinned as he turned shocked eyes on her. "Jesus," he said, chuckling. "Forgot how blunt you are."

Rhonda just smiled and pressed her thigh against his."That a bad thing?"

A queer little smile twitched at the edges of Dean's mouth. "Nah."

A small silence stretched in which Dean downed the rest of his beer.

"So, are you?" she asked.

He met her eyes for the first time that night, his own more brown than green and darkening. He didn't answer, persay, but inclined his head ever so slightly closer. Rhonda did the same and they moved toward each other slowly, gazes intimately locked. Rhonda brushed her lips against his, he tilted his head, and then they were kissing softly on her couch.

It was good. Dean's lips were soft and moist and his hands tucked themselves automatically in her hair. His tongue swiped against the seam of her mouth, slow and warm. It was good, of course it was, but Dean was stiff as hell. He bent his neck but not his back, forcing Rhonda to hold her head at an awkward angle. His hands were rigid and, opening her eyes, Rhonda found his brow furrowed and his face creased. It wasn't really the picture of a man enjoying a bit of necking with the promise of sex.

Irritated, she pushed a little harder at his lips to try to get his head in a better position. A little whimper escaped him, and his hands twitched.

Oh.

_Oh._

She caught his hair - shorter, now, and darker - while they kissed, giving the roots a violent tug to get him where she wanted him. Dean melted instantly. His shoulders slumped, his jaw fell slack, his knees bent, and a low moan caught in his throat. Everything about him screamed 'relief.'

Rhonda smiled and broke the kiss, grabbing his legs to pull them up on the couch so she could lean between them. Dean breathed heavily as she lay him down, her tiny hands groping at his chest.

"You haven't had this is a while, huh?" she asked him breathily, holding his head in place while she grinded her hip against his crotch. "Someone to take control, give you what you need?" Dean moaned in response, lips struggling toward hers. She could feel him already, rapidly hardening in his jeans, and rewarded him with her tongue in his mouth.

They made out for several minutes, Rhonda turning Dean's head to fit her needs and thrusting against his hardening length while Dean lay back with his hands on her ass and let himself be used.

Rhonda listened to his moans, beginning to breathe heavily herself at the sight he made. "God, you're so hot," she groaned, pulling his head back sharply. To his approving gasp, she moved down to kiss and bite at his throat. Dean's hips stuttered, rubbing himself desperately against her.

"You like that, baby?" Rhonda ground her knee down his dick to his balls, moving in circles. Dean's breath sped up in response.

Rhonda smirked against his neck, trailing her lips up to bite gently at his ear. "Yeah, you do. My pretty boy." She sucked hard on the lobe and Dean shuddered all the way down to his feet.

"Fuck...not..." he gasped, the first words he'd spoken since they began. "'M not..."

Rhonda pulled back from his ear with a slurp. Wow, this guy had some intimacy issues. Not that she was one to talk. "Not what? Not _completely fucking gorgeous_ right now? God, if you could see yourself..." Dean looked absolutely wrecked, all red lips, hooded eyes, and heaving chest, and he wasn't even naked yet. Speaking of which, she should probably change that. But first things first.

"You want me to fuck you?"

Dean froze, his eyes widening. Rhonda pressed her hips harder into him, wishing, not for the first time, that she had a real dick for him to feel grinding into him. She waited, but he was still just staring and breathing heavily, his cheeks flushed with color.

"Come on, Dean, tell me," she prompted, leaning down to brush her lips against his. "You want me to fill you up? Thrust a dick inside you? Make you come just from that with my panties stretched across your ass?" Dean swallowed, but didn't answer until she leaned down to whisper hotly in his ear, "I wanna bend you over this couch and fuck you 'til you scream, Dean, will you let me do that?"

Dean let loose with a breathy, shuddering groan and shook hard beneath her, suddenly desperate with his hands on her back. "Fuck, fuck...yes. God, yes, please..."

Rhonda grinned and kissed him fully, hooking her tongue in his mouth and dragging it slowly back out just to hear the noise he made. "Strip," she commanded. "I'll be right back."

She left him there and made her way leisurely to her bedroom. She hoped it looked leisurely, anyway. Inside she was giddy and jittery with anticipation. She hasn't pegged a guy in _years,_ not since her college days, and she still regrets not adding young, twinky Dean to the list. Cutting big guys with big egos down to their base elements was just as good, though.

Rhonda dug through her drawer of sex stuff (Hannah had called it the Wank Tank) until she found the blue silk bag with the _Lovehoney_ pattern. Crossing to the adjoining bathroom, Rhonda pulled out the toy to sanitize it.

Silicone and bubblegum pink, the 5-inch strap-on rested neatly in Rhonda's palm as she rubbed antibacterial soap into the shaft. Along with a padded harness, it also had a ribbed little butterfly at the base that would rest against her clit and a wicked hook at the tip that was perfect at finding a prostate. Best part? It fucking _vibrated._ Rhonda couldn't wait for Dean to find that out. After drying it off and checking the batteries, Rhonda rushed back to her room and stripped her clothes off. She considered the panties she was wearing for Dean, wondering if it was the panties themselves or the fact that she had previously worn them that got him off, but decided she had another pair he would look better in.

Rhonda peeled off the basic black boyshorts, a thin stream of slick stretching between her crotch and the material before it broke off. Woah, she was wetter than she thought.

Rhonda couldn't resist running a finger through it, spreading the warm wetness around and teasing at her clit. A pleased shiver travelled up her spine. Fuck, that felt good. She was tempted to keep going, to get off here and make Dean wait, but damn if waiting to come while she fucked him wasn't looking like a fantastically hot idea. Besides, the longer she spent in here, the more likely it was that Dean made a run for it.

Retracting her hand, Rhonda strapped the dildo on and tucked the remote out of sight. Then she gathered up a new pair of panties and a bottle of lube and padded back into the living room.

Dean was still there. He was stretched out on her couch, naked as the day he was born with a hand resting gently at the base of his still-hard cock.

Oh God, she swore she's seen him carved into the Parthenon. Pretty face, strong arms, and a soft little belly - the only difference between Dean and the hotties of Greek pediments was the kraken between his legs. And the freckles. Could he get any more perfect?

He sat up as she came in, his eyes darting between her bare breasts and the silicone cock jutting out between her legs as if he couldn't decide which he should be paying attention to. His cock gave a little jerk of appreciation.

"I never noticed you were bowlegged before," Rhonda noted, straddling his lap and slipping her arms coyly around his neck. The tattoo was new, too. "Kinda makes me think you were born to be fucked."

Dean breathed out shakily. "We gonna get to it? Wouldn't wanna waste my purpose in life." His lips spread in a cocky grin that was almost convincing enough to hide the tremor in his voice.

Rhonda smoothed her hands over his shoulders. "Eager," she commended, and kissed him. He leaned into it, sighing as she sucked his lower lip gently into her mouth.

God, this was going to be good.

Rhonda broke their mouths apart and slipped away to grab the [panties](http://www.lovehoney.com/product.cfm?p=23031), holding them up for Dean's approval. They were bright pink with black mesh triangles up the front and back. The ass was totally open, held together at three points with little satin bows.

Dean swallowed hard and licked his lips, but didn't start gathering his clothes and declaring he wasn't 'fucking queer' - she'd had that happen once. Rhonda counted it as a win, especially when Dean took the panties and put them on himself. He shuddered with what she hoped was arousal when his cock was confined beneath the stretchy material.

"You look good, baby," Rhonda praised. And mother of fuck, did he ever. She could see his half-hard cock curled up behind the mesh, stretching the material out. The panties would probably never fit her the same again, but Rhonda couldn't bring herself to complain. Dean lowered his eyes almost shyly, those enviously long eyelashes brushing his cheeks.

He was acting so _demure_ that Rhonda only felt it was fair to kick things into gear at last.

"Suck me," she ordered, sauntering over to where Dean sat on the couch and grabbing his hair in a firm fist.

Dean made a noise, his mouth opening in immediate compliance as Rhonda nudged the tip against his lips. He closed his eyes as he took it in, slowly working his perfect lips over the shaft like he'd been waiting for it all night.

"Such a good boy. You look so good with your perfect lips around a cock. You love it." She grabbed his face and began to move it back and forth, taking control of his movements. Dean's face was flushed and content under her ministrations, his mouth going slack in submission.

"More spit. Good boy. That's it, take it deeper now, just like you like it." She plunged deeper in, thinking maybe Dean could handle it to the back of his tongue before his throat opened up and she sank all the way in. _Holy shit._ "Swallow," she ordered, licking her lips. He did. _Holy fucking shit._

Rhonda pulled back so she could see the tip swell in Dean's cheek before thrusting back into his throat, repeating the action several times with no input from Dean but the occassional low groan.

When Rhonda finally pulled free of Dean's mouth he was red and shaky all over, eyes glazed and submissive, mouth wet and slack. His dick was straining against the panties and dripping a wet spot through the lace.

_Holy mother of fucking shit._

"Turn around, on your knees. Lean over the back of the couch." Dean did, breathing heavily through his mouth. His ass was left in the air, looking soft and pinchable in pink. Fuck, he looked good in those. The holes in the back of the panties allowed her teasing peeks at his crack, and Rhonda impatiently untied the center bows to reveal his twitching hole. She breathed over it gently as she spoke. "I can't wait to be buried deep in this ass. You'll be so tight, Dean." She spread lube over her fingers and very tenderly touched the pad of one to his rim. Dean mewled, his hips jerking forward immediately. Fuck, he was sensitive, how hot was that? Rhonda kept her finger in place, rubbing slowly as Dean gasped and shivered against her. She could see his fingers digging into his upper arms where they crossed beneath his head. Maybe too sensitive, actually. "Anyone ever do this for you before, Dean?"

He breathed deeply and began to push back against her finger, exhaling sharply as the tip sunk in. _Fuck._

"Dean, answer me," she reprimanded, pulling the finger back completely.

Dean whimpered and spread his legs wider in submission. "No, no, never," he whimpered. Rhonda rewarded him with the finger again, watching with growing desire as he fucked himself deeper on it. She got to pop Dean Winchester's cherry tonight and he was  _begging_ for it. This night was quickly catching up to the 'Tim Curry movies and sex' marathon with Lance Oakley, exercise science major, on level of hotness. Soon Rhonda's entire finger was swallowed in hot, slick tightness and _fuck_ but this man was sex on legs. She rotated her finger slowly to open him up, loving how the muscle clung to her, desperate for touch.

"Do you want another, Dean?"

"God, yes."

Rhonda added more lube and eased a second finger in, scissioring them quickly to Dean's obvious delight. He was clenching and shivering against her, his entire upper body writhing and shiny with sweat. His moans were loud - Rhonda thanked whatever angel was watching over her tonight that the woman who lived next door was off visiting with family this week. She'd gotten a lot of strongly worded letters about 'suspicious noises late at night'.

"Ready, Dean?" Rhonda asked, spreading her fingers wide so she could see inside his dripping hole. She watched it spasm as Dean groaned, gasping out an affirmative noise.

"I need a yes, Dean," Rhonda encouraged, twisting her fingers.

"Ah- yes, fuck yes, please!"

"Good boy." Rhonda pulled her fingers back, Dean whining at the emptiness, and slicked up the dildo. "Budge up, knees against the cushions." Dean straightened and shuffled forward until he was as far back into the couch as he could go, leaning his upper body over the back at Rhonda's gentle prodding.

"Thats my pretty boy," Rhonda cooed, stroking his back as she climbed on behind him. Dean shivered and pulled his ass up, the invitation clear. Rhonda grabbed his asscheeks roughly through the panties, rearing back to smack one cheek when she got a positive response. Dean was full of surprises - Rhonda only wished she got more than one night to be surprised.

She hooked her hands into the cleft of his ass and spread the cheeks apart, positioning the tip of the dildo at his hole and rubbing teasingly. Dean growled and tried to push back on her, but she held his ass tight. "Be a good boy and ask me nicely, Dean."

He turned his head to look at her, eyes dark and needy. "Please," he keened.

Well who was she to argue with that? Rhonda pushed in slowly until the toy was nestled all the way inside, Dean panting in audible little breaths the whole way down.

"How does it feel to be filled up, Dean? Good?"

Dean moaned. "Awesome."

Rhonda laughed, tucking her hair behind her ears. Damn, he looked good speared on her. "You haven't felt nothin' yet," she promised. She pulled back up with a skilled twist of her hips, this time scraping over Dean's prostate and he fucking _screamed._

"Fuck!" he yelled. "Oh, fuck, do that again."

Rhonda reached up to grip his hair, pulling his neck back. "What do we say, Dean?"

"Please," he begged. "Oh god, please fuck me."

Jesus Christ Rhonda might as well have come right then for all that sentence did for her. She obligingly thrust back in, relishing the noises Dean made. She fucked into him slowly, twisting her hip to drag against his sweet spot. It was really doing things to her watching the big man moan and writhe helplessly at the end of her dick, and Rhonda was really, really, needing some action for herself before she went crazy. She released Dean's hips, continuing to thrust in and out as she retrieved the remote from the back of the harness and cranked the dial to '1'.

The toy immediately came to life, buzzing against her and vibrating down the shaft to Dean. Rhonda gasped out a relieved moan and Dean barked out in surprise, throwing his head back with a needy howl that Rhonda simply _had_ to fuck him harder for.

Pleasure raced up and down her spine as the thrusting motions of her hips rubbed the wriggling butterfly against her clit. The pressure was building in her gut as she fucked in and out of Dean and the toy danced against her. She tried rocking from side to side between each thrust to increase the stimulation, and _oh dear sweet lord that was good._ Rhonda brought herself to the edge but pulled herself back, stilling for a moment to catch her breath before continuing to piston in and out of Dean's ass. Her clit got too sensitive to be touched after orgasm, and she really wanted Dean spilling himself over the vibrations.

"Ohh, god," Dean moaned. He was thrusting too, now, fucking himself wantonly on the silicone cock, his hands clenching and unclenching in the cushions.

Rhonda could relate. She cranked up the intensity with shaky fingers for both their benefits, The toy buzzing in quick little pulses that hit them both in just the right spots.

Rhonda began to quicken her pace, needing the extra movement. Fuck, she was close, she was so close. Warmth was swirling behind her groin, growing in ferocity as her vision grew darker. Rhonda slumped against Dean's back, pulling one leg up for more leverage to boost the snap of her hips and brought a hand around to press at Dean's erection, giving him something to thrust against. Dean was so going to come before her. He began to cry out with increasing urgency on every thrust in, building toward the same white-hot edge. This close to fucking heaven Rhonda's porn-mouth got away from her.

"You love this, don't you?" Rhonda growled. "You love being fucked, you fucking love it. You love being held down and thrust into just like this. You wanna be used. You want this hole of yours sloppy and red from being fucked so hard. Fucked so hard you'll walk funny for _days._ C'mon, baby, come. Come all over those fucking panties so I'll never be able to wear them again without remembering you begging for me like this. Come for me, let me see how much you love it."

Dean cried out and stilled his movements, shaking violently in the beginnings of orgasm. Rhonda suddenly wished they had done this the other way so she could see his face when he came. She squeezed his dick hard.

"That's my good boy, come, Dean, _come._ "

Dean did, arching his back and clawing at the couch as he filled the front of the panties. Rhonda could feel his dick throbbing and spurting cum beneath her palm, the material growling warmer and wetter. He babbled as he came, curses and noises and, once, Rhonda thought, a name.

Rhonda kept thrusing in and out of him while he came and rubbing herself on the pulsing toy. A few more rolls of her hips and Rhonda followed Dean over the edge and came hard, gasping and spasming. "Fuck, fuck, fuck, _Dean, oh!_ " She buried the toy in him to the hilt and continued to grind against the vibrations until they were both too sensitive to continue. Rhonda shut it off with trembling hands and pulled slowly out. Dean made a small noise of discontent, but slumped against the couch on his stomach, boneless. Rhonda slipped off the harness and flopped down next to him so they could both come down and catch their breath.

"You were right," Rhonda panted after a few moments.

"Uh?" Dean grunted, opening one eye.

Rhonda grinned. "That was 'awesome.'"

It was the brightest smile she'd seen from Dean all night.

* * *

She let him use the shower first; she figured he wanted to check himself out a little, anyway, and a man was best left with his own asshole in privacy. He returned in a towel - and he _was_ walking funny, Rhonda inwardly cheered - and they traded off, Rhonda rinsing and scrubbing herself and the toy quickly in hopes that Dean would still be there when she returned.

He was. Dean was standing near the arm of the couch, doing up his jeans and staring at the spot they had fucked on. Rhonda slowed her walk, noticing the renewed tension in his back and the distance he'd put between himself and the rest of the apartment. He looked tired and lost again, the Dean she'd seen in the last hour fleeing along with the time.

Rhonda suddenly wanted to ask who he'd been calling for when he came, but couldn't bring herself to do it. Instead she crept up behind him and wrapped her arms tenderly around his waist.

"The couch is new," she said. "The old one was too old and lumpy for any heavy use. Thanks for helping me break it in."

Dean huffed in amusement. His hands came up to squeeze hers, but also to break from the embrace. "Glad to," he replied, turning to face her with an almost shy expression.

Rhonda tilted her head to the side in consideration and cupped his chin in her hands to kiss him chastely. Dean's face was still guarded when he pulled back, and she waited for him to speak.

"I should go."

And there it was. The thing about pretty-boy drifters was that they never stayed for long. Apparently they sometimes came back a decade or so down the road, but Rhonda was hoping she would be unavailable for a booty call by next time. Despite her 'free love' policy, Rhonda was in her thirties now. She was getting too old for one night stands. She wanted to settle down. She missed Hannah.

"Yeah?" she murmured, not bothering to hide her disappointment.

"Yeah... I mean," he sighed. "It's just..." he gestured helplessly to her apartment, whatever words he wanted to say dying on his tongue. "I can't."

Rhonda nodded in understanding. "Well, I hope you get to be with whoever you can't be with now," she said softly. Dean looked surprised for a moment, something like grief shadowing his face, before smiling bitterly and shaking his head. "Yeah, well," he rasped, then cleared his throat. "You too."

Amusement curled in Rhonda's chest. Nothing gets past Dean Winchester, huh?

"You can stay the night, you know," Rhonda offered. Dean's eyes glittered at her uncertainly. "I guess, if your brother won't miss you for too long."

She smiled tentatively, holding out her hand for him to take. "Nothing weird, I promise, just..." She wondered whether to be honest, then thought to hell with it. "You look like you need some fucking sleep. And some company."

Dean hesitated, the hard new lines of his face siezing up in denial. Rhonda looked him in the eyes, willing him to remember how good it was to let her have control. Sex aside, she knew he  _needed_ this.

Eventually, Dean's shoulders relaxed and the wariness lifted from his eyes. "Okay." He slid his palm into her grip and let himself be led down the hall to Rhonda's room and the warmth and comfort of her bed.

He was gone in the morning, and Rhonda tried not to feel sad about it.

**Author's Note:**

> [Talk to me on tumblr!](http://www.cuddleslutdean.tumblr.com)


End file.
